100 Kink Challenge
by lola242
Summary: Phantom-doodles fanfic challenge (link can be found in my bio) Multiple Fandoms Multiple pairings.


100 Kink Challenge

Kissing – Dean/Jo

Warnings: Not really except Dean is older than Jo who is not underage and some bad language

Overview: During a casual game of truth or dare between Sam, Ash, Dean, and Jo it is discovered that Jo at the age of 22 has never been kissed. Something that Dean feels the need to remedy.

It was a slow month, no demonic omens, no witches, no yellow eyes, no Meg. The Winchester boys had wound up back at the Roadhouse, which had become somewhat of a basecamp. Dean assured himself had absolutely nothing to do with the sassy flirtatious blonde who he definitely had no feelings for. Even if he did, "wrong place wrong time" seamed to be their thing not that they had a _thing_ or at least any _thing_ Dean would allow himself to think about for any prolonged period of time.

This slow month in which Ellen offered the brothers a room above the roadhouse lead to Wednesdays becoming something of a drinking game night between Dean, Sam, Ash and Jo. On this particular Wednesday clad in empty beer bottles, Sam nursing a bottle of Jack and plenty of plaid Dean came up with the ever so brilliant, in his mind, game of spin the bottle truth or dare. Jo was a master of the poker face, how else would she get by hustling regulars? But at the suggestion her guard faltered only slightly of course Dean noticed. "Unless your nervous about us hearin' all your dirty little secrets princess" dean teased with a wink. As quickly as her face fell it was right pack in place as she said, "I think you should be worried about confessing your big ol' crush on me Dean-o." Deans ears grew a little redder but he decided it best to not say anything, "Lets play. Whoever spins asks the questions, person it lands on has to answer truth or dare and take a shot. Deal?" There were no major complaints from the already buzzed participants.

Being the youngest Jo was first to spin. Sam being the first victim chose dare over truth and was made to give a 60 second strip tease which he pulled off quite confidently along with a shot of his bottle of Jack. Next Sam's spin landed on Dean who went for truth, "But dude I already know everything about you!" to which Dean replied "thems the rules little brother ask me a question already." Sam shot an exasperated look in the direction of Jo and Ash who weren't really paying much attention at this point. "Fine! Have you ever hit a home run with a different species, ya know like demon angel shifter?" Dean took his shot of gin before confessing a pretty graphic and awkward story about a shifter chick he brought back from a bar one night. After a stunned awkward silence dean spun the bottle landing on Ash. The game went on for several more rounds and several more shots both questions and answers getting racier as the night progressed, with the exception of Jo who kept opting for dare instead of truth. Finally Dean spun the bottle in the direction of Jo who was nearly about to say truth before getting cut off by a slightly drunk Dean, "No, no, nonono little miss hunter warrior princess you've done dare for like 300 rounds nono time for a truth." Jo kept her poker face stone considering the amount of tequila she had ingested and just how nervous she became. Dean continued, "How many dudes have you bagged from the Roadhouse." Jo's mind went blank, shit, shitshitshit. "Well um. Uh. None?" She quickly took a swig from her bottle of tequila trying to focus more on the burning going slowly down her throat rather than weather or not Dean would let it go. Sadly he didn't, "Hold up you mean none from roadhouse or never gotten with any guy ever?!" Jo didn't want to look up, she was so confident but no one knew that not only was she a 22 year old virgin, Jo had never kissed a boy before. She was all bark and no bite. There wasn't a lot of opportunity in her line of work and she had never found the right guy- until she realized she had the major hot's for Dean. Not that she would admit it to anybody, her self probably number two on the list right after Dean. The room was quiet now. She would have to answer eventually. "uh no I've um… never even kissed anybody." An awkward silence had settled over them. Any rounds were pointless afterwards and they decided to call it a night.

Jo quickly ran up the stairs to take a shower and brush her teeth before bed. Oh man that had to be the most embarrassing moment of her life. She grimaced at herself in the mirror. Absently leaving the bathroom she didn't notice dean standing at the door and walked full speed into his toned chest. "Oh shit man sorry I didn't see you I was… never mind um... Night" Dean had caught her after the collision one hand on her strong shoulder the other on her slim curved hip. After several seconds of processing what she had said and where his hands fell on her body he quickly pulled back his hands in an awkward flailing motion. Why was it he could be mister cool mister suave mister one night stand normally but when it came to the petite blonde it was like he couldn't function. He nodded as Jo brushed past him and towards her room. He turned quickly to add, "Hey Jo! Actually I wanted to uh- apologize about earlier I didn't mean to make you feel bad or whatever I just uh didn't realize. Um… anyway sorry." He finished lamely. She allowed a small smile nodded and continued to her room determined to not let the blush slowly creeping on to her tanned skin show. She leaned against her door and allowed herself to let out a breath she hadn't realized she was holding. Suddenly there was a low knock on the door. She opened it confused to see Dean on the other side. "ah… Shit um… I was just thinking uh… I mean I know its all wrong place wrong time but… If you wanted I could er- would like to be er- if you want…." Uh get it together man. But before he could get any more of his stupid speech about wanting to be her first kiss because he cared about her out, there were soft pink lips against his. After the initial shock he slowly wrapped his hands around her, one against small of her back the other just lightly threaded through her hair. She rest her hands gently and somewhat awkwardly on his hips. She smiled against his lips. After pulling away she looked into his beautiful green eyes, kissed him once more and said, "thank you Dean." Then closed the door again. They would have to discuss what this meant, maybe, or maybe not. But Dean hoped that she would want there to be more firsts together, luckily on the other side of the door Jo was sitting on her bed with a grin on her face thinking the exact same thing.


End file.
